N-Aminomorpholine → HCID 66740466, 화합물

HRID 1627279노트

반응식

HRID 1627279 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([S:32]([NH:35][C:36](=[O:40])OCC)(=[O:34])=[O:33])=[CH:27][C:26]=3[F:41])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:42][CH3:43].[NH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:41])=[CH:27][C:28]([S:32]([NH:35][C:36](=[O:40])[NH:44][N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)(=[O:34])=[O:33])=[CH:29][C:30]=3[F:31])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:42][CH3:43]

참가 물질

5

반응물 2

HCID 20315N-AminomorpholineHCID 66739854Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate

생성물 1

HCID 66740466HCID 66740466, 화합물수율 46.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate (76 mg, 0.12 mmol, 1.0 eq) and 4-aminomorpholine (0.045 mL, 0.46 mmol, 4.0 eq) in toluene (2.5 mL, anhyd) were heated at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water, followed by brine. After drying (MgSO4), the organics were concentrated and purified by chromatography (silica, 0 to 80% EtOAc/Hex, then 10% MeOH/DCM) to provide the title compound (40 mg). 1H NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 7.41-7.16 (m, 4H), 7.03-6.90 (m, 3H), 6.57-6.43 (m, 4H), 4.02-3.98 (m, 2H), 3.71-3.65 (m, 3H), 3.57-3.50 (m, 3H), 3.48-3.38 (m, 1H), 3.31-3.25 (m, 1H), 2.69-2.58 (m, 3H), 1.46 (s, 6H); MS (EI) m/z 710.1 (MH+).

후처리

  1. temperatureat reflux for 2.5 h
  2. washwashed with water
  3. dry with materialAfter drying (MgSO4)
  4. concentrationthe organics were concentrated
  5. custompurified by chromatography (silica, 0 to 80% EtOAc/Hex

출처 및 근거

ORD 기록
ord-81b4184b03ee480ca010d837eeca4a6e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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